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Photosensitive polymer, resist composition, and associated methods

a technology of resist composition and polymer, applied in the direction of photosensitive materials, instruments, photomechanical equipment, etc., can solve the problem of dry etching resistance of a photosensitive resin

Active Publication Date: 2009-06-18
CHEIL IND INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0005]Embodiments are therefore directed to a photosensitive polymer, a resist composition, and associated methods,

Problems solved by technology

The most representative problem is dry etching resistance of a photosensitive resin.

Method used

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  • Photosensitive polymer, resist composition, and associated methods
  • Photosensitive polymer, resist composition, and associated methods
  • Photosensitive polymer, resist composition, and associated methods

Examples

Experimental program
Comparison scheme
Effect test

synthesis example 1

Synthesis of 4-(naphthalen-2yl)hepta-1,6-dien-4-ol

[0073]

[0074]A 4-(naphthalen-2yl)hepta-1,6-dien-4-ol monomer was synthesized according to the method as in shown in Reaction Scheme 2.

[0075]First, 16 g of 2-naphthaldehyde was dissolved in 150 mL of THF, and 150 mL of allyl magnesium chloride (a 2.0 M THF solution) was slowly added thereto. The resulting mixture was reacted at a temperature of about 45° C. for 8 hours. After the reaction, the reactant was slowly neutralized in an extreme amount of thin hydrochloric acid solution. Then, the extract was extracted therefrom using diethyl ether and purified through column chromatography (hexane:ethyl acetate=3:1), preparing 10 g of 4-(naphthalen-2yl)hepta-1,6-dien-4-ol monomer (yield: 42%).

synthesis example 2

Synthesis of a 4-(naphthalen-1-yl)hepta-1,6-dien-4-ol)monomer

[0076]

[0077]A 4-(naphthalen-1-yl)hepta-1,6-dien-4-ol monomer was synthesized according to the same method as in shown in Reaction Scheme 3.

[0078]The 4-(naphthalen-1-yl)hepta-1,6-dien-4-ol 2 was prepared according to the same method as in Synthesis Example 1 using 1-naphthaldehyde instead of 2-naphthaldehyde (yield: 40%).

example 1

Synthesis of a Photosensitive Polymer

[0079]25 mmol of the monomer according to Synthesis Example 1 and 5 mmol of V601 (Wako Pure Chemicals Industries Ltd.) as a polymerization initiator were dissolved in a MEK (methyl ethyl ketone) solvent (in a double weight of the entire weight of the monomer). The solution was degassed using N2 gas for about 30 minutes and then, stirred at 80° C. Next, 40 mmol of 2-ethyl-2-adamantyl methacrylate (EAMA) and 35 mmol of γ-butyrolactonyl methacrylate (GBLMA) were dissolved in a small amount of THF. This solution was slowly dropped to the above resulting product for about one hour. The mixture was polymerized for about 4 hours.

[0080]After the polymerization, the reactant was slowly precipitated in an excess of diethylether solvent. The precipitate was filtered and then dissolved in THF and reprecipitated in diethylether. The acquired precipitate was dried in a 50° C. vacuum oven for about 24 hours, yielding a polymer represented by following Formula 6...

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Abstract

A photosensitive polymer, the photosensitive polymer including repeating units represented by Formulae 1 to 3:wherein R1 and R3 are independently hydrogen or methyl, R2 is a C4 to C20 acid-labile group, R4 is a lactone-derived group, AR is a substituted or unsubstituted phenyl ring, or a substituted or unsubstituted aryl having from two to three fused aromatic rings, carbon CAR is bonded directly to an aromatic ring of AR, l, m, and n are positive integers, 1 / (l+m+n) is about 0.1 to about 0.5, m / (l+m+n) is about 0.3 to about 0.5, and n / (l+m+n) is about 0.1 to 0.4.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]Embodiments relate to a photosensitive polymer, a resist composition, and associated methods.[0003]2. Description of the Related Art[0004]For a photoresist material used to produce fine patterns, a deep-UV (deep UV) resist material using a shorter wavelength such that provided by an ArF excimer laser (193 nm) may be preferred to a resist material using a longer wavelength such as that provided by a KrF excimer laser (248 nm). For example, forming a semiconductor device with a capacity of more than 16 gigabytes needs a pattern size of less than 70 nm according to a design rule. As a result, a resist film may be thinner and have a reduced process margin for underlayer etching. The most representative problem is dry etching resistance of a photosensitive resin.SUMMARY OF THE INVENTION[0005]Embodiments are therefore directed to a photosensitive polymer, a resist composition, and associated methods, which substantially overc...

Claims

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Application Information

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IPC IPC(8): G03F7/004C08F24/00G03F7/20
CPCG03F7/0397C08F24/00Y10S430/106Y10S430/111G03F7/0045G03F7/0392
Inventor CHOI, SANG-JUNCHO, YOUN-JINSHIN, SEUNG-WOOKKIM, HYE-WON
Owner CHEIL IND INC